Hometown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Hometown Vacation
An easy way to experience this city is with a customized Hometown vacation package. Base yourself in the neighborhood of The Loop, which is great for bars and pubs, history and festivals or go someplace else — our package deals are all about you. Eager to venture out and explore? SeatGeek Stadium, Chicago Ridge Shopping Mall and Trinity Christian College are just a few of the most popular places to visit during your trip to Hometown. Browse Expedia's wide range of travel options and start organizing your ultimate vacation to Hometown today.
Top Hometown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel 505 River North
Downtown Chicago
CA $1,216
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (2,924 reviews)
The hotel's location is good but the staff made the stay great. Everyone was very helpful at the desk when I needed to make changes. The intersection that the hotel is near can get trashy due to multiple bars and restaurants but the property was kept very clean. We had a very good stay and would stay again in future trips.
Reviewed on Oct 13, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
CA $1,226
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (3,105 reviews)
The space is adequately clean, you’ll have to personally inform the front desk should you prefer housekeeping to do their rounds in your unit. Staff were kind and accommodating. The location is accessible to bus stops just right across the entrance and another few blocks away.
Reviewed on Oct 13, 2026
Ready to book your vacation to Hometown?
Hometown Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $166
CA $197 total
Nov 5 - Nov 6
includes taxes & fees
8/10 Very good! (10,178 reviews)
"Old rooms and a lot carpets"
Reviewed on Oct 13, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $217
CA $258 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (5,534 reviews)
"I absolutely loved this place. Close to everything and great view"
Reviewed on Oct 12, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $204
CA $242 total
Nov 3 - Nov 4
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
What to do in Hometown
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Hometown vacation package cost?
You'll find cheap prices from CA $1,216 on Expedia for your Hometown getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Hometown costs.
What are the cheapest months to go to Hometown?
You can generally find lower prices and better availability in January, February and November. Browse our cheap Hometown vacation packages and you could score some great off-season discounts.
How many days is enough for Hometown?
Hometown vacations can be as short or long as you like, but to really sink your teeth into this destination, we'd suggest 2 days is a good ballpark. With this timeframe, you can visit major attractions like Moraine Valley Community College Fine and Performing Arts Centre and Lake Katherine Nature Centre along with underrated gems. Don't forget to visit cool neighbourhoods such as Archer Heights and Clearing either. If you're clever with your time, you can even schedule a day trip from Hometown too.
How to find the best Hometown package deals?
Finding a cheap Hometown package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Hometown package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Hometown vacation as a package?
You can enjoy significant savings on your Hometown retreat by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Hometown?
If you have your Hometown travel dates confirmed, book early to score some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Hometown?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Hometown.
- Set your budget: Consider costs such as flights, meals and transportation when calculating how much to set aside for your trip to Hometown. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a lavish retreat.
- Decide how many days away: Start by making a list of all the attractions you want to experience in Hometown. Then, estimate how long you'll need for each, including any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Hometown vacation package.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
